EP 1687250 A1 20060809 - PROCESS FOR PRODUCING OPTICALLY ACTIVE 3-(4-HYDROXYPHENYL)PROPIONIC ACIDS
Title (en)
PROCESS FOR PRODUCING OPTICALLY ACTIVE 3-(4-HYDROXYPHENYL)PROPIONIC ACIDS
Title (de)
VERFAHREN ZUR HERSTELLUNG VON OPTISCH AKTIVEN 3-(4-HYDROXYPHENYL)PROPIONSÄUREN
Title (fr)
PROCEDE DE PRODUCTION D'ACIDES 3-(4-HYDROXYPHENYL)PROPIONIQUES OPTIQUEMENT ACTIFS
Publication
Application
Priority
- JP 2004017998 W 20041126
- JP 2003398201 A 20031127
Abstract (en)
[origin: WO2005051882A1] The present invention relates to a process for producing an optically active 3-(4-hydroxyphenyl)propionic acid useful as intermediates for medicines, through short steps in good yield and with high optical purity. More specifically, the present invention relates to a process for producing an optically active 3-(4-hydroxyphenyl)propionic acid of the formula (6): wherein R<2> is an alkyl group; R<5> to R<8> are each independently a hydrogen atom or a substituent; and the symbol * is an chiral carbon atom, or a salt thereof, which comprises reacting a benzaldehyde of the formula (1): wherein R<1> is a protective group; and R<5> to R<8> are each the same as defined above, with a glycolic acid derivative of the formula (2): wherein R<3> is a hydrocarbon group; and R<2> is the same as defined above, hydrolyzing the resulting product to give a cinnamic acid of the formula (4): wherein R<1>, R<2> and R<5> to R<8> are each the same as defined above, or a salt thereof, and subjecting the resulting cinnamic acid (4) or a salt thereof to asymmetric hydrogenation to give an optically active phenylpropionic acid of the formula (5): wherein all the symbols are each the same as defined above, or a salt thereof, followed by deprotection.
IPC 8 full level
C07C 51/36 (2006.01); C07C 51/09 (2006.01); C07C 51/41 (2006.01); C07C 51/43 (2006.01); C07C 59/64 (2006.01)
CPC (source: EP US)
C07C 51/09 (2013.01 - EP US); C07C 51/36 (2013.01 - EP US); C07C 51/412 (2013.01 - EP US); C07C 51/43 (2013.01 - EP US); Y02P 20/55 (2015.11 - EP US)
Citation (search report)
See references of WO 2005051882A1
Designated contracting state (EPC)
CH DE ES FR GB IE LI
DOCDB simple family (publication)
WO 2005051882 A1 20050609; EP 1687250 A1 20060809; JP 2007512222 A 20070517; US 2007142472 A1 20070621
DOCDB simple family (application)
JP 2004017998 W 20041126; EP 04819490 A 20041126; JP 2006520429 A 20041126; US 57874404 A 20041126